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methyl 2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)nicotinate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
42%
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃; for 1h;Microwave irradiation;
101111 Step la. To a solution of ethyl 2-fluoronicotinate (0.15 g, 0.97 mmol) in NMP (0.5 ml..) was added diisopropylethyl amine (0.50 mL, 2.9 mmol), and 8-oxa-3- azabicyclo[3.2.Iioctanc (0.17 g, 0.72 mmol). Thc resulting mixture was irradiated with microwaves (100C) for lh and loaded directly onto a silica column. Eluting the column with EtOAc/hexanes (0-100%) provided methyl 2-(8-oxa-3-azabicyclo[3.2.l]octan-3- yl)nicotinate as a clear oil (0.100 g, 42% yield). MS (ES) for C13H1(,N203: 249 (MW).
methyl 2-(3-fluoro-5-methoxyphenylamino)nicotinate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
0.293 g
2-Fluoronicotinic acid methyl ester (0.4 g, 2.58 mmol) and <strong>[2339-58-4]3-fluoro-5-methoxyaniline</strong>(0.354 ml, 3.09 mmol) were heated by microwave irradiation at 120 C for 50 mm. 0.1 ml(0.873 mmol) of <strong>[2339-58-4]3-fluoro-5-methoxyaniline</strong> was added and the mixture was irradiated for 30mm at 120 C. Some DCM was added and the mixture was washed twice with H20. Organicphase was dried over Na2SO4, filtered and evaporated. Crude product was purified bytrituration with diethyl ether. 0.293 g of the title compound was obtained.?H NMR (400 MHz, DMSO-d6) 6 ppm 3.78 (s, 3 H) 3.91 (s, 3 H) 6.48 (dt, 1 H) 6.96 (dd, 1H) 7.03 - 7.11 (m, 1 H) 7.42 (dt, 1 H) 8.29 (dd, 1 H) 8.48 (dd, 1 H) 10.20 (s, 1 H).
With lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; at 0℃;Reflux;
Add <strong>[78473-00-4]4-amino-3,5-dichlorobenzonitrile</strong> (1.86 g, 10 mmol) and dioxane to a 100 mL single-mouth vial(40 mL), 14 mL of LiHMDS/THF solution (14 mmol, 1 mol/L) was slowly added dropwise at 0 C, and after stirring uniformly, the compound of formula (3) (1.38 g, 11 mmol) of dioxane solution was slowly added dropwise ( 10mL), after the addition is completed,Warming up to reflux reaction14h. After the TLC monitoring reaction was completed, the reaction was quenched by the addition of saturated aqueous ammonium chloride (10 mL).The crude product was separated by silica gel column chromatography (V petroleum ether: V ethyl acetate = 1:1)1.82 g of the compound of the formula (5) was obtained in a yield of 56.8%.
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